How do you add an SSL certificate or what is needed to make an HTTPS connection to a web server?

When I click New Remote Server, I am able to successfully connect to my remote server with http://ipaddress:3142 as the address and Microsoft User/Password authentication. However, I receive the following error when trying to connect with https://ipaddress:3143

Connection Error : An error occurred while sending the request.

Notes:

My remote server is a VM through Microsoft Azure. The VM was created with the Warewolf ESB, so the HTTP: TCP/3142 and HTTPS: TCP/3143 inbound security rules are all in place. Also, I can successfully connect to my localhost machine from the remote server with both HTTP/HTTPS.